Kyle and Jess's Engagement Free Dining Report! Pics Galore...UPDATE: OCT. 27th

How awesome to get to propose at the most magical place on earth. I'm sure she was thrilled. Can't wait to hear about it and the food of course!
 
Congrats!! What a great place to propose. Looking forward to the reading how you popped the question.

Looking forward to reviews. especially, chefs. we are eating there friday for the first time. oh, and sci fi too - on sunday. (1st time in a loooong time)

We love Kona - hope you did too. Have to skip it this trip to try some new places.

Happy wedding planning!
 

Ok the food reviews are coming but it seems like a lot of you want to hear about our proposal so here it is!

I knew right away I wanted to propose at Disney for a variety of reasons. First and foremost let’s face it; Disney is the most magical place on earth, who wouldn’t want to be engaged at Disney. Secondly, Disney is the place where dreams come true; is there truly a better place to propose to the girl who made all my dreams come true?

When it came time to plan how I was going to do it I kind of hit a road block. A few years ago my brother proposed to his now wife in front of the Castle on Main Street. Though this was very nice I knew right away it wasn’t the way I would drop to one knee.

I had a few thoughts including the wishing well, on a ride, on poly beach, etc…but none of them made it easy to capture the special moment on camera. For those who haven’t seen me on the boards before I’m an avid photographer and I’ll admit I’m behind the lens more than in front of it resulting in a very limited number of pictures together with Jess.

Randomly I had a vision that somehow I could contact Disney and set up a Caricature artist to draw an image of me prosing to jess. After a little bit of research I was able to find the contract company that Disney uses for their caricatures. I contacted them with my idea and they happily accepted my idea.

After about a month of communicating, submitting pictures, and describing details to the artist he put together a perfect Caricature of me proposing to Jess.
FinishedPhoto.jpg


The only thing left between the artist and myself was to plan a time/date and how we would pull off the surprise. I chose the first day of our trip, September 14th at the wilderness lodge. I had a few options on the location but given that our plans were to hit Downtown Disney early on the 14th and the Magic Kingdom in the afternoon I figured I could use the wilderness lodge as a stepping stone before taking the boat to MK.

Prior to leaving I made a few phone calls to Disney to make sure they had our proposal on all of our Dinning ADR’s but not on our Room Reservation. After confirming with three different cast members on three different days my proposal secret wasn’t anywhere on our room reservation. Keep in mind I was proposing the afternoon of our check in, hence leaving it on the ADR’s.

Flash forward to September 14th….

We checked into All Star Music and we were more than half way through the check in routine when the cast member goes “So I see you guys are celebrating a recent proposal”….My heart dropped and I had visions of my plan going out the window and I was going to drop down on one knee right there in the Hotel lobby. Somehow though I held it together and was able to convince the cast member there had to be a mistake. I went on and on about how Jess was with me when I booked the trip and we didn’t say anything like that. I also did this little joke about how I’d love to but sadly I didn’t have a ring and if someone FedEx’ed one down I would gladly do it. It somehow worked!

We arrived at the Wilderness Lodges around 4:15pm and I made a suggestion to Jess that we get a Caricature done to hang in our Future home as we didn’t have too many unique souvenirs from our Disney trips. Luckily she thought it was a great idea and I was very relieved to see no one getting their caricature done when we arrived. As previously directed by the artist I was to act like a new dumb customer. We Discussed prices (I had pre ordered/paid before our trip) and looked through his book and finally chose a “fake” pose.

We each took our turns sitting in the hot seat as he drew our fake picture. The plan was to have him make a fake image as a decoy and when he was done we would turn around and he would switch the fake image out with the real one. Well come to find out he drew a really nice fake image that actually took 30mins.

He finally finished and asked for my camera to capture our reaction (this was pre planned as well). At this time we turned around and he swapped out the fake picture for the real one. He told us to turn around and there was the drawing of me proposing to Jess. After giving her a quick moment to take in the picture I dropped down on one knee and ask her to marry me, she said YES in shock.

Here are the pictures from our special moment:

DSC_0054.jpg


DSC_0055.jpg


DSC_0057.jpg
 
Ok that is so darn beautiful that I cried...and I am so mad at the CM for almost ruining your surprise!

So is there a Disney wedding in the picture?

DH wants to renew our vows on our 20th..guess where? At the WL in one of the little rooms on the 4th floor overlooking the water..so pretty!

Just 13 more years to go!

Wishing you both many years of happiness!
 
That was such a lovely proposal! It was perfect and unique! Congrats to you guys. You're a cute couple. :goodvibes


And darn that CM, almost ruining everything! I'm glad it pulled through. :)
 
congratulations! and very unique idea that showed a lot of thought ... so good job :thumbsup2


... gotta say, given that it was your first day, it's really good she said yes, otherwise that would be a really awkward rest of your vacation :goodvibes
 
Lovely story about your proposal and such a sweet, thoughtful way of popping the question! I'm glad it all worked out OK. :goodvibes Thanks for sharing and congratulations!
 
Awesome Proposal....so romantic and with the unique personal touch....
congratulations!
 
Congrats on the engagement, what a unique and creative way to propose. Can't wait to hear more.
 
That was such a beautiful story thank you so much for sharing that with us. Also I have to add that the same thing happened to my now fiance when we checked in. He was planning on proposing the night we got there during Illuminations and he set up a private dessert party for just the two of us. Well during check in they handed him the "Were Engaged" pins and were like "Congratulations" but luckily he had a feeling something like that was going to happen and he sent me to look around the resort,PORS so I had no idea anything happened but needless to say he was pretty mad that they almost ruined all of his work and could have spoiled the surprise. But luckliy everything worked out and im very glad to hear that you were able to play it off so well.
 





New Posts










Save Up to 30% on Rooms at Walt Disney World!

Save up to 30% on rooms at select Disney Resorts Collection hotels when you stay 5 consecutive nights or longer in late summer and early fall. Plus, enjoy other savings for shorter stays.This offer is valid for stays most nights from August 1 to October 11, 2025.
CLICK HERE













DIS Facebook DIS youtube DIS Instagram DIS Pinterest

Back
Top